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Upstream product

• 45849-05-6 2,3-bis(hydroxymethyl) bicyclo [2,2,1] heptane 
• 16529-77-4 exo-tricyclo<4.2.1.0^2,5>nonan-3-one 
• 6004-79-1 (exo)-Hexahydro-4,7-methanoisobenzofuran-1,3-dione 

Relevant academic research and scientific papers

A Proton-Responsive Pyridyl(benzamide)-Functionalized NHC Ligand on Ir Complex for Alkylation of Ketones and Secondary Alcohols

A Cp*Ir(III) complex (1) of a newly designed ligand L1 featuring a proton-responsive pyridyl(benzamide) appended on N-heterocyclic carbene (NHC) has been synthesized. The molecular structure of 1 reveals a dearomatized form of the ligand. The protonation of 1 with HBF4 in tetrahydrofuran gives the corresponding aromatized complex [Cp*Ir(L1H)Cl]BF4 (2). Both compounds are characterized spectroscopically and by X-ray crystallography. The protonation of 1 with acid is examined by 1H NMR and UV-vis spectra. The proton-responsive character of 1 is exploited for catalyzing α-alkylation of ketones and β-alkylation of secondary alcohols using primary alcohols as alkylating agents through hydrogen-borrowing methodology. Compound 1 is an effective catalyst for these reactions and exhibits a superior activity in comparison to a structurally similar iridium complex [Cp*Ir(L2)Cl]PF6 (3) lacking a proton-responsive pendant amide moiety. The catalytic alkylation is characterized by a wide substrate scope, low catalyst and base loadings, and a short reaction time. The catalytic efficacy of 1 is also demonstrated for the syntheses of quinoline and lactone derivatives via acceptorless dehydrogenation, and selective alkylation of two steroids, pregnenolone and testosterone. Detailed mechanistic investigations and DFT calculations substantiate the role of the proton-responsive ligand in the hydrogen-borrowing process.

Metal-catalysed Enantiospecific Aerobic Oxidation of Cyclobutanones

The metal-catalysed aerobic oxidation of substituted racemic cyclobutanones provides optically active lactones with enantioselectivities of up to 95percent e.e.

IMPROVED PROCEDURE FOR LITHIUM BOROHYDRIDE REDUCTION OF CYCLIC ANHYDRIDES TO LACTONES IN TETRAHYDROFURAN

The rate of reduction of several cyclic anhydrides by lithium borohydride in tetrahydrofuran at 25 deg C has been studied.The reaction has been utilized for the rapid and selective conversion of cyclic anhydrides to lactones.